trifluoro-1,3,5-triazine

• ChemBase ID: 126782
• Molecular Formular: C3F3N3
• Molecular Mass: 135.0474096
• Monoisotopic Mass: 135.00443168
• SMILES: Fc1nc(F)nc(F)n1
• Canonical SMILES: Fc1nc(F)nc(n1)F
• InChI: InChI=1S/C3F3N3/c4-1-7-2(5)9-3(6)8-1
• InChIKey: VMKJWLXVLHBJNK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trifluoro-1,3,5-triazine
• IUPAC Traditional name: cyanuric fluoride
• Synonyms: trifluorotriazine; 2,4,6-trifluoro-s-triazine; cyanuryl fluoride; Cyanuric fluoride; 2,4,6-Trifluoro-1,3,5-triazine; Cyanuric fluoride; 2,4,6-三氟-1,3,5-三嗪; 三聚氟氰

Database IDs

• CAS Number: 675-14-9
• EC Number: 211-620-8
• MDL Number: MFCD00014597
• Beilstein Number: 124237
• PubChem SID: 24857237; 162221110
• PubChem CID: 12664
• Chemspider ID: 12143
• Wikipedia Title: Cyanuric_fluoride

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.7186153
• LogD (pH = 7.4): 1.7186153
• Log P: 1.7186153
• Molar Refractivity: 25.1124 cm^3
• Polarizability: 7.5072546 Å^3
• Polar Surface Area: 38.67 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: colourless liquid
• Melting Point: −38 °C; -38°C
• Boiling Point: 73-74°C; 74 °C
• Density: 1.574; 1.574 g/cm^3
• Refractive Index: 1.3840

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: XZ1750000
• European Hazard Symbols: Corrosive (C); Highly toxic (T+)
• UN Number: 3389; UN3389
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; I
• Risk Statements: 24-26-35; R24, R26, R35
• Safety Statements: 20-26-27/28-36/37/39-45; 26-28-36/37/39-45; S26, S28, S36/37/39, S45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H310-H314-H330; H310-H330-H314-H318
• GHS Precautionary statements: P260-P280-P284-P302 + P350-P305 + P351 + P338-P310; P260-P303+P361+P353-P304+P340-P305+P351+P338-P320-P361-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3389 6.1/PG 1

Product Information

• Purity: ≥97.0% (GC); 98%
• Empirical Formula (Hill Notation): C3F3N3

DETAILS

Sigma Aldrich - 28625

Caution
can precipitate on storage
Other Notes
Modifies tyrosyl residues in proteins1,2; Reagent used for the preparation of carboxylic fluorides3,4
Packaging
10, 50 g in glass bottle

REFERENCES

• In combination with pyridine, converts carboxylic acids to acyl fluorides in high yields under mild conditions: Synthesis, 487 (1973). Similarly, protected (Fmoc) amino acids are converted in dichloromethane solution to amino acid fluorides. tert-Butyl ester and ether groups are also stable under these conditions. The resulting acyl fluorides are more stable to water than the corresponding acyl chlorides but are more reactive to amines, thus providing a useful peptide coupling method: J. Am. Chem. Soc., 112, 9651 (1990); Tetrahedron, 50, 5309 (1994); Appendix 6. For use of Fmoc amino acid fluorides in solid-phase peptide synthesis, see: Tetrahedron Lett., 32, 1303 (1991); J. Org. Chem., 59, 3275 (1994). For a review of peptide synthesis via amino acid halides, see: Acc. Chem. Res., 29, 268 (1996).
• Carboxylic acids can be converted to alcohols under mild conditions via the acyl fluoride and reduction with NaBH₄ in the presence of MeOH. The method can be carried out in one pot and is applicable to N-protected amino acids and peptides for which other reduction methods are unsuitable: J. Org. Chem., 61, 6994 (1996).
• Reagent for deoxygenation of alkyl sulfoxides, cf Cyanuric chloride, L03442: Synthesis, 221 (1980), and for dehydration, at room temperature in DMF, of Boc amino acid amides to nitriles: Tetrahedron. Lett., 38, 4221 (1997).